Mike Matheny and his current financial troubles are an example in wondering what athletes are thinking when they choose to invest money or buy “stuff” in an effort to “diversify” or “make their money work for them.”

The Cardinals manager’s issues came to light over the past few days as a court ruling went against him, potentially wiping out his entire net worth. According to this piece on StLToday.com, Matheny’s goal of making a post-career living in real estate fell flat to the tune of owing $4.4 million and not having the cash or assets to pay it off. We saw Curt Schilling go through a larger-scale nightmare last year and it’s still ongoing as he’s selling his bloody sock among other memorabilia.

The reasoning behind people making unwise financial decisions that could compromise them for years if not for the rest of their lives is presented as preparing for the future. They can happen to anyone and are not a reason to ridicule. Matheny gave a viable explanation with the following (from the above-linked post):

Matheny’s interest in real estate started before he joined the Cardinals in 2000 to be their catcher.

He had been released by Milwaukee and, then, quickly thereafter, Toronto. He was 29.

“I stunk, and saw a bad trend happening in my career,” he said.

Matheny, however, nursed a long interest in real estate, and he started taking correspondence courses while playing ball. “Guys used to give me grief. I was doing homework while we were on the flights.

“I had four kids at the time, and I knew I hadn’t really done enough in the game to just sit back and do nothing,” he said.

Fair enough. He was finding other avenues to earn a living. But the same logic that stated that he needed to take real estate courses and find a post-baseball career should have said to him that the house he built with the amenities listed in the piece were unnecessary. The house had:

17 rooms

Indoor batting cage

Home theater

Pool with a water slide and a private lake with a floating golf green in the middle

Most of the money he made in baseball was earned in the last five years of his career. With the Cardinals, he surpassed $1 million in salary for the first time in 2002 when he made $2.5 million. Over the next two seasons—his final years with the Cardinals—he made $7.25 million.

Matheny signed a 3-year, $10 million contract with the Giants after the 2004 season. He retired after the second of the three years due to post-concussion syndrome and his 2007 salary isn’t listed on his Baseball-Reference page, but because his career ended due to injury and he retired, presumably he got paid for the final year. His career earnings are probably higher than the listed amount of $18.729 million to the tune of another $4.65 million.

That would make over $23 million.

Also, a Major League player has ancillary income from their road per diem—AKA meal money. Clubs aren’t checking to see what players spend it on; they could go to McDonald’s for breakfast and lunch and pocket the leftover cash; plus they’re fed from an elaborate post-game spread after each game, leaving dinner a luxury and not a necessity.

They receive post-season shares, which Matheny got in 2001, 2004 and 2005; there are rights fees for images and other lesser-known streams of money coming in. Usually, the amount of money is negligible in comparison to their salaries, but for younger players or journeymen as Matheny was before he got to the Cardinals, it’s not.

In short, if a player wants to be frugal and save what will eventually come to a lot of money, he can do it.

MLB players must play 43 days in the majors to earn a minimum $34,000 annual pension plan. Just one day in the majors gets them lifetime healthcare coverage. After 10 years in the big leagues, benefits grow to $100,000 annually.

Matheny spent 13 years in the big leagues.

So here’s the question I have to ask of Matheny and Schilling and any other player who blew a massive amount of money on business schemes: How much is enough? Could he not live on the amount of money he made in his career and the $100,000 per year he receives as a pension with free healthcare and the cachet that comes from living in St. Louis and having been a former Cardinals’ player? From the juice that the words, “I played in the big leagues,” have everywhere?

This isn’t simply a personal issue for Matheny. The Cardinals knew about this when they hired him as a surprise choice to replace Tony LaRussa. The players’ comments regarding this coming out were supportive, but that’s not guaranteed to last if the team starts playing poorly.

Matheny had on-field success in 2012, reaching game 7 of the NLCS before being eliminated. By standard assessment, he did a good job because the team won. But in reality, Matheny was functioning with LaRussa’s players; with the freedom of diminished expectations after the departure of the future Hall of Fame manager LaRussa; the best pitching coach of this generation, Dave Duncan; and the best hitter in baseball, Albert Pujols. His rookie strategic gaffes were expected and understandable for a first time manager at any level and could easily be glossed over by the bottom line fact that the team won and came within a game from a second straight pennant.

But how long is the player support going to last? How long will the mistakes be taken as learning on the job when Matheny has to actually do something other than stand in the corner of the dugout, look managerial and let the players play?

If the team is struggling, will his financial missteps be referenced as sapping his concentration and commitment to the team? Knowing how players are, if a pitcher is unhappy with being pulled from a game, will he turn around and whisper to his teammates, “Maybe if I pay off his debts, he’ll leave me in.” Will there be resentment from Matheny himself at the lofty salaries the players, who are essentially his underlings, are making? Will he roll his eyes and think about a hitter batting .220 and being paid $5 million? It’s a human reaction that can set the charges to blow the place up.

The Cardinals are transitioning from LaRussa’s team to something else. They won’t function on cruise control forever and it’s when Matheny has to manage that his evolution will be clearer. He might learn on the job, but he might get swallowed up by its magnitude and what has to be done post-LaRussa/Duncan/Pujols—things he might not be capable of doing.

Matheny’s own statement that it was the money he owed which spurred his return to baseball is also a potential issue. Whether it was what he intended or not, it sounds as if he’s implying that he’s doing the Cardinals a favor by managing the team and if his real estate goals didn’t go bust, he’d have left baseball in the rear view mirror on his way to becoming a real estate titan.

There are a number of ways for this to go and a lot of the “if then, then that” can lead to a dark place for the Cardinals. It might wind up amounting to a personal financial situation that’s being handled legally, but ends up permeating the job he’s trying to do now, festering negatively, and turning in a direction that few will be willing to openly discuss, but is there nonetheless and isn’t going to go away.